Explore top 2025 5 Star Hotels in Crestwood

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Top Crestwood 5 Star hotels

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$431 nightly
The price is $506 total per night from Nov 2 to Nov 3
$506 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...
9.4/10 Exceptional! (1,730 reviews)
"Clean room. Great staff"

Reviewed on Oct 2, 2025

Opens in a new windowTrump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$544 nightly
The price is $638 total per night from Nov 2 to Nov 3
$638 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.6/10 Exceptional! (1,012 reviews)
"Y"

Reviewed on Sep 21, 2025

Opens in a new windowThe Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$650 nightly
The price is $763 total per night from Nov 2 to Nov 3
$763 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...
9.6/10 Exceptional! (1,013 reviews)
"Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely ..."

Reviewed on Sep 27, 2025

Opens in a new windowThe Peninsula Chicago
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$530 nightly
The price is $622 total per night from Nov 2 to Nov 3
$622 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...
9.4/10 Exceptional! (1,005 reviews)
"Was very clean, although the toilet wasn’t flushing properly overall a great experience"

Reviewed on Sep 18, 2025

Opens in a new windowFour Seasons Hotel Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
11 E. Walton Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$582 nightly
The price is $684 total per night from Nov 3 to Nov 4
$684 total
Nov 3 - Nov 4
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...
9.2/10 Wonderful! (1,006 reviews)
"Simply love this hotel"

Reviewed on Sep 18, 2025

Opens in a new windowWaldorf Astoria Chicago
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
800 N Michigan Ave, Chicago, IL
$574 nightly
The price is $674 total per night from Nov 3 to Nov 4
$674 total
Nov 3 - Nov 4
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.4/10 Exceptional! (999 reviews)
"My wife and I spent an incredibly enjoyable weekend at the hotel. It is within walking distance to many different points of interest in the heart of the Magnificent Mile. The service, amenities, and stay were memorable. We will definitely return."

Reviewed on Sep 29, 2025

Opens in a new windowPark Hyatt Chicago
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$525 nightly
The price is $616 total per night from Oct 30 to Oct 31
$616 total
Oct 30 - Oct 31
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...
9.2/10 Wonderful! (729 reviews)
"Well appointed rooms with great service. The restaurant is decent too; there are also abundant dining options nearby that are open even on Labor Day."

Reviewed on Sep 25, 2025

Opens in a new windowNobu Hotel Chicago
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
160 E Pearson Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$460 nightly
The price is $540 total per night from Nov 2 to Nov 3
$540 total
Nov 2 - Nov 3
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...
9/10 Wonderful! (1,006 reviews)
"Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one."

Reviewed on Sep 15, 2025

Opens in a new windowThe Ritz-Carlton, Chicago
The St. Regis Chicago

The St. Regis Chicago

5 out of 5
401 East Upper Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
$625 nightly
The price is $734 total per night from Oct 5 to Oct 6
$734 total
Oct 5 - Oct 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...
9/10 Wonderful! (77 reviews)
"Clean room, amazing view"

Reviewed on Sep 7, 2025

Opens in a new windowThe St. Regis Chicago
Art Villa

Art Villa

5 out of 5
467 N Armour St, Chicago, IL
$680 nightly
The price is $848 total per night from Oct 12 to Oct 13
$848 total
Oct 12 - Oct 13
Total with taxes and fees
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. ...
10/10 Exceptional! (2 reviews)

Reviewed on Aug 12, 2025

Opens in a new windowArt Villa
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Crestwood Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Crestwood to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Crestwood 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Crestwood before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Crestwood hotel reviews by fellow wanderers

Warwick Allerton - Chicago

Warwick Allerton - Chicago

5 out of 5
Posted 11 hours ago
Travelocity Verified Review
"We chose this hotel due to location, and previous stays there."
A verified traveler stayed at Warwick Allerton - Chicago
Warwick Allerton - Chicago

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